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H7779

Sigma-Aldrich

Retinoic acid p-hydroxyanilide

≥95%

Synonym(e):

4-HPR, Fenretinide, N-(4-Hydroxyphenyl)retinamide

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About This Item

Empirische Formel (Hill-System):
C26H33NO2
CAS-Nummer:
65646-68-6
Molekulargewicht:
391.55
MDL-Nummer:
MFCD00792674
UNSPSC-Code:
12352106
PubChem Substanz-ID:
24278472
NACRES:
NA.77

Biologische Quelle

synthetic (organic)

Qualitätsniveau

200

Assay

≥95%

Form

powder

Farbe

yellow to yellow-orange

Lagertemp.

−20°C

SMILES String

CC1=C(\C=C\C(C)=C\C=C\C(C)=C\C(=O)Nc2ccc(O)cc2)C(C)(C)CCC1

InChI

1S/C26H33NO2/c1-19(11-16-24-21(3)10-7-17-26(24,4)5)8-6-9-20(2)18-25(29)27-22-12-14-23(28)15-13-22/h6,8-9,11-16,18,28H,7,10,17H2,1-5H3,(H,27,29)/b9-6+,16-11+,19-8+,20-18+

InChIKey

AKJHMTWEGVYYSE-FXILSDISSA-N

Verwandte Kategorien

Allgemeine Beschreibung

Retinoic acid p-hydroxyanilide is a synthetic analog of retinoid.

Anwendung

Retinoic acid p-hydroxyanilide has been used:
  • as a synthetic retinoid to induce apoptosis in SEB-1 sebocytes
  • as a medium supplement for C2C12 myoblasts to test its effect on ceramide formation
  • to test in cytotoxicity in T-cell acute lymphoblastic leukemia (T-ALL)

Biochem./physiol. Wirkung

Retinoic acid p-hydroxyanilide, also called fenretinide, increases reactive oxygen species, activates caspases and induces apoptosis. It also inhibits dihydroceramide desaturase, leading to a decrease in ceramide biosynthesis. Fenretinide may elicit anticancer activity in cultured human breast cancer cells. It acts as an insulin antagonist and may be useful in treating insulin resistance. Fenretinide or 4-HPR has chemotherapeutic potential and is cytotoxic to retinoic acid-resistant cancers.
Vitamin A acid analogue with antiproliferative activity; induces apoptosis in malignant hemopoietic cell lines.

Piktogramme

Exclamation markHealth hazard
GHS07,GHS08

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Analysenzertifikate (COA)

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Matthew J Watt et al.
Endocrine reviews, 40(5), 1367-1393 (2019-05-18)
The liver is a dynamic organ that plays critical roles in many physiological processes, including the regulation of systemic glucose and lipid metabolism. Dysfunctional hepatic lipid metabolism is a cause of nonalcoholic fatty liver disease (NAFLD), the most common chronic
C Marth et al.
Journal of the National Cancer Institute, 75(5), 871-875 (1985-11-01)
The synthetic retinoid 4-hydroxyphenylretinamide (HPR) showed antiproliferative effect on cultured human breast cancer cells, which were sensitive to retinoic acid (RA) too. Investigation of the cell cycle by flow cytophotometry showed a significant increase of cells in the S-phase of
D Delia et al.
Cancer research, 53(24), 6036-6041 (1993-12-15)
N-(4-Hydroxyphenyl)retinamide (HPR) is a synthetic retinoid of particular clinical interest in cancer chemoprevention. We have examined the in vitro effects of HPR on lymphoid and myeloid malignant cell lines and found that at concentrations between 10(-5) and 3 x 10(-7)
Claude Lachance et al.
Infection and immunity, 82(5), 1778-1785 (2014-02-20)
Streptococcus suis is an important swine pathogen and an emergent zoonotic pathogen. Excessive inflammation caused by S. suis is responsible for early high mortality in septic shock-like syndrome cases. Polyunsaturated fatty acids (PUFAs) may contribute to regulating inflammatory processes. This
Chunxiao Wang et al.
Biochemical and biophysical research communications, 493(4), 1555-1559 (2017-10-11)
In the absence of approved therapeutics, Zika virus (ZIKV)'s recent prolific outbreaks in the Americas, together with impacts on unborn fetuses of infected mothers, make it a pressing human health concern worldwide. Although a key player in viral replication in
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Artikel

Retinoic Acid and Gene Expression

All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apoptosis, and embryonic development.

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